Synthesis of new sugar amino acid derivatives of D-glucosamine

Carbohydrate Research

Volumn 338, Issue 5, 2003, Pages 399-406

  Xie, Juan ^a  

^a Centre National de la Recherche Scientifique   (France)

Author keywords

2 Acetamido 2 deoxy D glucose; Amino C glycosyl compounds; Sugar amino acids

Indexed keywords

GLUCOSE; SUGARS; SYNTHESIS (CHEMICAL);

ACETOLYSIS;

AMINO ACIDS;

AMINO ACID DERIVATIVE; BENZYL DERIVATIVE; CHEMICAL COMPOUND; GLUCOSAMINE; GLUCOSE DERIVATIVE; GLYCOCONJUGATE; N ACETYLGLUCOSAMINE; SUGAR;

ARTICLE; CARBOHYDRATE SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; INFRARED RADIATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; THIN LAYER CHROMATOGRAPHY;

ACETYLGLUCOSAMINE; AMINO ACIDS; GLUCOSAMINE;

EID: 0037436010     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(02)00487-1     Document Type: Article

References (46)

1. Kennedy J.F. Carbohydrate Chemistry. 1988;Oxford University Press, Oxford.
2. Bahl O.P. An Introduction to Glycoproteins. 1992;Marcel Dekker, New York.
3. Kobata A. Acc. Chem. Res. 26:1993;319-324.
4. Arsequell G., Valencia G. Tetrahedron: Asymmetry. 10:1999;3045-3094.
5. Taylor C.M. Tetrahedron. 54:1998;11317-11362.
6. Haltiwanger R.S., Kelly W.G., Roquemore E.P., Blomberg M.A., Dong L.Y.D., Kreppel L., Chou T.Y., Hart G.W. Biochem. Soc. Trans. 20:1992;264-269.
7. Wells L., Vosseller K., Hart G.W. Science. 291:2001;2376-2378.
8. Zachara N.E., Hart G.W. Chem. Rev. 102:2002;431-438.
9. Reviewed in Xie J. Recent Res. Devel. Org. Chem. 3:1999;505-523.
10. Cipolla L., La Ferla B., Lay L., Peri F., Nicotra F. Tetrahedron: Asymmetry. 11:2000;295-303.
11. SanMartin R., Tavassoli B., Walsh K.E., Walter D.S., Gallagher T. Org. Lett. 2:2000;4051-4054.
12. Yang G., Franck R.W., Bittman R., Samadder P., Arthur G. Org. Lett. 3:2001;197-200.
13. Ohnishi Y., Ichikawa Y. Bioorg. Med. Chem. Lett. 12:2002;997-999.
14. Wakabayashi T., Shiozaki M., Kurakata S. Carbohydr. Res. 337:2002;97-104.
15. Pachamuthu K., Gupta A., Das J., Schmidt R.R., Vankar Y.D. Eur. J. Org. Chem. 2002;1479-1483.
16. Knapp S., Myers D.S. J. Org. Chem. 66:2001;3636-3638.
17. Postema M.H.D. Tetrahedron. 48:1992;8545-8599.
18. Levy D.E., Tang C. Baldwin J.E., Magnus P.D. The Chemistry of C-glycosides. 1995;Elsevier Science, Oxford.
19. Du Y., Linhardt R.J. Tetrahedron. 54:1998;9913-9959.
20. Nicotra F. Top. Curr. Chem. 187:1997;55-83.
21. For recent reviews on this subjet, see: (a) Gruner, S. A. W.; Locardi, E.; Lohof, E.; Kessler, H. Chem. Rev. 2002, 102, 491-514;(b) Schweizer, F. Angew. Chem., Int. Ed. 2002, 41, 230-253.
22. For recent reviews on this subjet, see: (a) Gruner, S. A. W.; Locardi, E.; Lohof, E.; Kessler, H. Chem. Rev. 2002, 102, 491-514;(b) Schweizer, F. Angew. Chem., Int. Ed. 2002, 41, 230-253.
23. Irvine J.C., McNicoll D., Hynd A. J. Chem. Soc. 11:1911;250-261.
24. Heyns K., Paulsen H. Chem. Ber. 88:1955;188-195.
25. Fodor G., Otvos L. Chem. Ber. 89:1956;701-708;
26. Yoshimura, J.; Sato, T.; Ando, H. Bull. Chem. Soc. Jpn. 1969, 42, 2352-2356.
27. Müller C., Kitas E., Wessel H.P. J. Chem. Soc., Chem. Commun. 1995;2425-2426.
28. Wessel H.P., Mitchell C.M., Lobato C.M., Schmid G. Angew. Chem., Int. Ed. 34:1995;2712-2713.
29. Suhara Y., Hildreth J.E.K., Ichikawa Y. Tetrahedron Lett. 37:1996;1575-1578.
30. Suhara Y., Ichikawa M., Hildreth J.E.K., Ichikawa Y. Tetrahedron Lett. 37:1996;2549-2552.
31. Graf von Roedern E., Lohof E., Hessler G., Hoffmann M., Kessler H. J. Am. Chem. Soc. 118:1996;10156-10167.
32. Hoffmann M., Burkhart F., Hessler G., Kessler H. Helv. Chim. Acta. 79:1996;1519-1532.
33. Burkhart F., Kessler H. Tetrahedron Lett. 39:1998;255-256.
34. Sofia M.J., Hunter R., Chan T.Y., Vaughan A., Dulina R., Wang H., Gange D. J. Org. Chem. 63:1998;2802-2803.
35. Ghosh M., Dulina R.R., Kakarla R., Sofia M.J. J. Org. Chem. 65:2000;8387-8390.
36. Kobertz W.R., Bertozzi C.R., Bednarski M.D. J. Org. Chem. 61:1996;1894-1897.
37. Xie J. Eur. J. Org. Chem. 2002;3411-3418.
38. Grugier J., Xie J., Duarte I., Valéry J.M. J. Org. Chem. 65:2000;979-984.
39. Roe B.A., Boojamra C.G., Griggs J.L., Bertozzi C.R. J. Org. Chem. 61:1996;6442-6445.
40. Cui J., Horton D. Carbohydr. Res. 309:1998;319-330.
41. McDevitt J.P.; Lansbury Jr., P.T. J. Am. Chem. Soc. 1996, 118, 3818-3828.
42. Henry W.R., Weinreb S.M. J. Org. Chem. 58:1993;4745.
43. Mbongo A., Fréchou C., Beaupère D., Uzan R., Demailly G. Carbohydr. Res. 246:1993;361-370.
44. Xie J., Molina A., Czernecki S. J. Carbohydr. Chem. 18:1999;481-498.
45. Shao H., Wang Z., Lacroix E., Wu S.-H., Jennings H.J., Zou W. J. Am. Chem. Soc. 124:2002;2130-2131.
46. Wong C.H., Moris-Varas F., Hung S.C., Marron T.G., Lin C.C., Gong K.W., Weitz-Schmidt G. J. Am. Chem. Soc. 119:1997;8152-8158.